Trial and Error
by xXxLadyFreakyStyleyxXx
Summary: Modern Day College AU in which David has a hard time trying to create the perfect date for Emery and him. It wouldn't be so hard if it wasn't for the fact that he had no idea where to start and if his friends weren't ones who enjoyed watching him suffer. DavidOC Oneshot


**If you like this story and you haven't read my other Newsies story Girls Can Sell Papes Too! give it quick peek, you might like it if you end up liking this one too, Enjoy! ^^**

Trial and Error: A Newsies Fanfiction

"What do you mean you don't know where to take her?" Spot asked him in disbelief.

David looked down at the table and flicked a crumpled straw wrapper off the table, flattening his hair in embarrassment. He didn't find any encouragement from his friend Jack who laughed openly as he leaned back in his chair and shook his head at his poor friend. It was bad enough he needed dating advice but it was even worse because he had to go through the awkward situation that was asking Spot Conlon for advice on where to take his best friend on a date. The curly haired boy stiffened noticeably under Spot's severe gaze.

"_Well?_" He asked again, crossing his arms impatiently.

David let out a sigh and propped his chin on his elbow before facing the shame. Spot looked at Jack with inquisition but only got a shrug in return.

"I don't know where to take her!" He blurted out in frustration before slouching in his chair and crossing his arms across his chest.

Spot rolled his eyes and exhaled in disappointment. Jack leaned forward and put a hand on David's shoulder in support. It had only been a month and a half since he and Emery had become couple and they had only gone on one official date and evidently it didn't end so well. The day after when they were selling papers she ended up spilling it to Kid Blink when they happened to bump into each other and he felt so bad for David he leaked the bad news to him before the end of the day. David was distraught at first but afterwards he wanted so badly to find out why she didn't like it.

"What happened with the one place you took her too, what was it-" Jack was interrupted when Spot suddenly put a hand up.

Jack and David looked at him curiously while he drummed his finger tips together, leaning back in his chair with his eyes closed before he opened them sharply and sat up all of a sudden.

"Maybe it's not where you took her, maybe it's what you _did_." Spot said in a subtle but menacing manner.

David swallowed lightly before blushing a bright red while Jack cackled uncontrollably as he slumped over in his seat. Spot looked more and more threatening the longer he remained silent but David couldn't help it because of how stunned he was by the mere insinuation what was being implied.

"N-no, Kid said it was specifically w-where I took her." He stuttered, desperate to make Spot stop glaring at him.

Spot still looked a little skeptical but eased up a bit and leaned back in his chair with his glass in his hand. He took a long sip and let out a refreshed sigh as he near finished the drink and let his eyes flicker around for a waitress to give him a refill. David was a little nervous that he still had the wrong impression but he was able to relax a little with out the harsh stare being directed at him. Spot wasn't a very big guy and a little shorter than David too but what he lacked in muscle and height he made up for in intimidation and iron-clad tenacity. He did lead Brooklyn after all.

"So where'd you take her?" Jack asked through a mouth full of burger.

After David rolled his eyes at his friends awful table manners he told him about the date. "I took her to see that new action flick, Godzilla. Everybody at school kept ravin' about it so I asked her if she'd go and she said 'yeah' so we went."

Jack nearly choked on his food and Spot groaned in frustration as he shook his head and closed his eyes. David looked at them both in inquiry at their reactions, what was so wrong with that? He knew Emery liked action-y movies like the Marvel movies and such, so he didn't think it was that bad an idea. Apparently he was wrong otherwise Kid wouldn't have had to bare the bad news of his 'hit and miss'.

"Come on Davey! Even _you _can't be this dense." Spot moaned before he bit off a piece of his chicken and chewed it in irritation.

"What're you talkin' about?" David demanded, he was getting a little tired of Spot dogging him.

"You _never_ take a girl to a movie for the first date." Jack clarified after swallowing his food. "Too quiet, and it always makes for an awkward situation if the girl is the type that doesn't like to be disturbed when she watches a movie in theaters."

"Which she _is_," Spot added in a matter-of-fact tone. "Nice goin' Davey."

David could've kicked himself but instead he let his jaw drop at the information he was given. He didn't think he could've felt more stupid than he did in that moment. How could he NOT know that about Emery, they had been together for a good amount of time so you would think he would know something as simple as that. Jack chuckled lightly and gave David a pat on the back before taking another bite out of his food. David picked up his glass and finished off the rest of his Coke before setting it down and putting his head onto the table. He had to make up for this some how other wise he'd have to keep dealing with Spot and Jack's wise cracks which he would never hear the end of when they eventually got to other newsies.

0-0-0-0-0-0-0-0

"I can't believe it, tell me again how you got tickets to a Broadway show at the concert hall on a Saturday night David?" Emery inquired with a brow raised as they got off the bus and walked down the sidewalk.

Since their last date had been an apparent bust David decided to take her to something he knew she'd like. There was a showing of The Sound Of Music at 8 o' clock that night which happened to be one of the only musicals she liked so he saved up for a few days and snagged them some decent seats for the show to surprise her. Emery was pleasantly surprised by the tickets and was happy to go with him, he could only hope she'd have a better time on this date.

"I told you, I saved up for them and had semi-good timing." He joked casually, even though he was more nervous than he was on their first date.

She giggled quietly, her nose crinkling ever so slightly like it always did when she laughed. He always thought it was an endearing quality, trivial as it may seem to others. He squeezed her hand gently and grinned down at her as her laughter died down. Emery gave him a small squeeze back as they slipped through the crowd at the front of the concert hall. Once inside David led her to their section and an usher showed them to their seats.

"This place is so fancy..." Emery mumbled as they sat down, looking around at the grandiose concert hall.

David chuckled nervously at the comment and looked around with her. They weren't as well dressed as some of these other people but it wasn't required of attendees to wear formal attire so he didn't feel the need to put that unnecessary pressure onto Emery. This date was supposed to be better and he knew she hated getting dressed up when she could help it so he decided not to tell her.

"And really big too." He added as he looked up at the ceiling, the domed roof seemed to go on forever.

The lights on the stage blinked a few times before dimming a little bit which effectively silenced a majority of the audience to a whisper in the various conversations. He felt Emery loop her arm through his and he smiled to himself as she leaned on his shoulder.

"Hey didn't your sister drag Jack here once?" She asked with a reminiscent chuckle.

David laughed openly at the memory but quieted almost as soon as he did because of the stares and occasional shushes he got from people around them. He slouched a little in his chair while Emery tried not to snicker at his misfortune. He had forgotten how strict people were about being quiet in the theater, he hoped it wouldn't be a downer on the outing because if he botched this one he'd never hear the end of it from Spot. The Brooklyn newsie leader wasn't exactly thrilled about him dating his child hood friend so if he disappointed her again Spot would not hesitate to reprimand David nor spare his feelings.

"Yeah he did, she wanted to see Wicked real bad and it was her birthday so there really wasn't much Jack could do." He said, considerably more quiet.

Emery chuckled lightly and shook her head. "Good man, I feel sorry for him though. My sister loved Wicked so I got my fill of it when we were kids."

"Really?" He asked, a brow raised in interest.

Before she could answer the lights shut off and the ones on the stage lit up as the curtain parted. It was an abbey like the ones that nuns live in, the set people had done a really good job with the props and the scenery on the back drop. They even had a virgin Mary statue in the center of the court yard of the abbey, that must've taken a lot of work.

"Nice props, huh?" David mentioned off-handedly.

Emery was about to reply when they were shushed harshly by some irritated audience members behind them. They both shrunk a little in their seats and looked ahead to the stage to watch the play as the lead entered stage left. She had a marvelous singing voice but David was more concerned about the lack of communication between him and Emery. She hadn't liked the last date because they weren't able to talk to each other and apparently, according to Spot, she didn't liked to be talked to while she watched a movie. As the play went on and the silence continued, David had a bad feeling growing in his stomach.

0-0-0-0-0-0-0

"So you bombed it, again." Spot said bluntly while lining up his pool stick.

Jack rubbed his neck and sighed heavily as he walked back over to the couch where his poor friend had his head in his hands. David groaned as he heard Spot's amused chuckling coupled with the sounds of billiard balls clacking together as they rolled across the pool table. The curly haired newsie was starting to get a little worried. What if it wasn't the dates she didn't like? What if it was him?

"What exactly was the probably wit this one?" Jack asked as he leaned back onto the couch to put his feet up.

David sighed. "At least this time she told me to face there was a problem."

Kid Blink scoffed and rolled his eyes as he lined up his shot. "Oh quit your cryin' Davey, I just _happened_ to run into her that day I told you like a million times."

Jack and Spot chuckled openly at Kid's remark while David remained un-amused as he slouched in his seat.

"So what did she say was wrong?" Jack asked once again, not bothering to hide his curiosity or his impatience.

David groaned as he shook his head. It was the same thing that she didn't like about the last date and the worst part was...it was the same reason _he _ended up disliking the date by the time the night was over. He thought maybe they would be able to communicate more freely since it was musical but apparently the people who go to see musicals have even less tolerance than movie goers which didn't seem possible at first but he sure learned by the end of the show.

"Quit leavin' me in suspense Dave!" Jack persisted as he nudged his friend a little roughly.

"It was the same problem as last time." David muttered, avoiding eye contact with everybody.

"Really?" Kid chipped in with blatant surprise in his tone.

Spot laughed even louder than before as he sat himself down in a chair while Kid took another shot. David really wished he could've had this talk with Jack in private, more specifically anywhere that Spot Conlon wasn't. Emery and Spot had been friends ever since they were kids in Ireland which meant he knew everything about her. Unfortunately, now that he was dating Emery this also meant Spot was almost always the first person to know about his botched dates.

Almost.

He had convinced Emery that some things were private about their relationship obviously, that and he didn't need Spot teasing him about every little thing. Apparently this didn't stop her from telling some of their other friends about it but he couldn't blame her for wanting to confide in someone else about this sort of thing instead of complain to him. He could appreciate that she wanted to spare his feelings but there were some things he needed to know.

"Well what are you gonna do now, huh Davey?" Jack inquired as David got up to get a glass of water.

He was about to reply but Spot decided to generously offer up his point of view once again.

"Here's a million dollar idea; take her to do somethin' she actually likes." The Brooklyner stated matter-of-factly.

Jack snickered only slightly but silenced himself when he started to get a death glare from David as he nursed his glass of water across the room in the kitchen. Kid Blink chuckled lightly only to interrupt himself with a groan as his shot missed it's intended target and Spot pushed him aside to take his own shot. He _had _been taking her to things she liked doing but maybe they weren't working because he hadn't found the right thing to do for a date.

"Why don't you try takin' her to get somethin' to eat?" Jack suggested as David made his way back to his original place on the couch.

David nodded in agreement as he thought about any possibility of this going wrong. It was simple enough so maybe it was exactly what he needed.

0-0-0-0-0-0-0-0

Emery felt her stomach flip as the familiar sound of an old dodge engine wafted through her open window. She looked at herself in the mirror and frowned slightly as she took one last once over of what she was wearing. David had come into the circulation center the other day spouting about how he finally had enough money saved up for a date for them at this new sushi house in their neighborhood. The only downside was that for some reason the joint required a dress code for all attendants which meant she had to get all fancied up to eat raw fish and sea weed. How messed up was that?

She wasn't ungrateful, in fact she almost lost all her breath as he told her about it with his blue eyes shining with anticipation and a dopey but hopeful grin on his face as he finished pitching the idea to her. When he finally did finish she kissed him despite all the hoots and hollers they got from the other newsies because she was so happy that he would go to all that trouble but it wasn't until the end of the day that he remembered to mention that formal wear was a requirement.

"Oh David." She sighed in slightly exasperation as she looked at herself.

Medda had lent her a figure fitting, calf-length, short sleeved, black dress with white polka dots and a pair of dark red heels for the occasion and demanded she wear her fake string of pearls and put a jade pin in her bright copper curls. Emery had drawn the line at make up and nails but she ended up softening up just a little and let Medda talk her into wearing light red lipstick. She heard familiar little foot falls rush up the stairs and toward her room and almost as if on cue the Swedish Meadow Lark burst through the door with an eager smile.

"Emery do NOT make him wait down there all by himself! The poor baby!" The vaudeville singer urged with a sympathetic lilt in her voice as she pushed Emery toward the door.

Medda was persistent as she pushed the red headed newsie down the stairs, not taking into account that Emery had almost tripped three times by the time they reached the floor. The older woman giggled quietly to herself as she shooed Emery toward the door way that led to the front porch where David was waiting for her. She gave her a cheeky grin before rushing up the stairs leaving the girl newsie to stare at the door way. She took a deep breath and grasped the cool metal of the knob and quickly stepped outside the door and shut it before anyone else could harass her.

"Oh...wow." A breathless but all too familiar voice sounded behind her.

Emery swallowed lightly and turned to see David standing on the bottom step of her stoop in a full press suit with a baby blue tie that almost perfectly matched his eyes which she couldn't help but notice were glowing as he looked at her. She blushed furiously and quickly glanced away from him and tried to say something in return to that but she shut her mouth so as not to look like more of a moron. In a moment he was up the steps and placing his soft lips on her cheek in a quick kiss. Emery finally looked up at him and managed a small kiss on the lips before he led her down the steps and toward his car, a grin shamelessly adorning his face. He opened the door for her and just as he was about to close the door she opened her mouth to say something.

She hesitated for a moment before finally spitting it out. "Y-you look very handsome David."

He smiled even wider before leaning down and giving her a drawn out kiss on the lips before shutting her door and making his way toward the driver's side. As they drove out of her neighborhood and into the city he had a good feeling about the way things were looking. This date was going to be the one. He knew it.

0-0-0-0-0-0-0-0

Jack sighed heavily as the sound of a baseball hitting the wall sounded one time after another in a sort of melancholy kind of rhythm which was ironic because it definitely matched the mood in the living room of their shared apartment. Spot was sitting expressionless with eyes full of exasperation as he watched David intently while the poor blue eyed newsie continued to throw his baseball against the wall. After only a minute more of this Spot growled low in his chest before standing abruptly and grabbing the baseball and hurling it out the open window.

"Spot!" David yelled in anger as he went to the window.

"Get another one." Spot retorted, not hesitating to let his irritation seep into his voice.

David grimaced at the Brooklyner and was about to hit him when he realized that would be a very _very _bad idea in the long run and sat down by the window before he could do anything stupid. What really got to him was the fact that he was just as angry and annoyed as Spot was, the only difference was that Spot put his blame solely on David's shoulders which only multiplied his already growing frustration.

"Ok this is ridiculous, there's no way you coulda botched this one Davey we went over it four times!" Jack shouted before throwing himself onto the couch and letting out a groan into the cushion.

"I told you two dopes _not _to make her get all dressed up!" Spot yelled back as he made his way toward the window. "I told you _not _to take her to a fancy schmancy restaurant, it would only make her nervous I says but did anybody listen? NO."

David scoffed at the boy and tuned out the abuse that was getting spewed at him as he tried to think of what exactly went wrong for her. She seemed happy to go when they left her house, albeit nervous, but still excited. It was only when they got to the place that she started to shut down on him and things played out the same way all the other dates had gone; uncomfortable silence. He loved Emery but his patience was running thin and so was his cash.

"I don't see what Davey did wrong." Jack defended sitting up on the couch and not even flinching when Spot glared at him.

"That kind of situation puts too much pressure on her and keeps her from getting comfortable, _that's_ why she shut down on you Dave." Spot rebutted, walking back to where Jack was on the couch.

Looking back on the whole night David did notice she had started to look particularly nervous once they got inside, the atmosphere was so sophisticated and elite but he thought he had been doing a good job keeping her mind off of all that. Evidently he didn't because when they had left she was so relieved to be out and pleaded with David to never take her to a place like that ever again. She was grateful that he went through all that trouble but it was a fruitless gratitude to him because he knew he had struck out...again.

"Listen Davey, don't be flashy." Spot offered in a calmer tone as he sat down on the couch. "Take her somewheres pleasant and for God's sake David make it a place where you can actually talk to each other."

Both boys looked at him with wide eyes as he continued to offer his advice to David. Although Spot was annoyed with his constant failures, he didn't want David to keep striking out with Emery because he wanted her to stay with him. David was good for her and he could tell she genuinely liked him too. The poor sap had struck out so much he started to pity him so maybe it was time to help him out.

"Keep it simple. Take her to a baseball game, a walk by the harbor, a vaudeville show, and whatever you do don't make a big deal out of it." Spot finished, leaning back into the cushions and putting up his feet on the coffee table.

David hadn't though of it that way before. He figured the more effort he put into making the date as high class as he could that it would make it full proof but that wasn't the case at all. Emery just wanted to be able to be comfortable with him in a romantic environment. What really mattered was that the both of them had fun together so now he was gonna follow Spot's advice and keep it simple. Hopefully, he would be able to pull it off too.

0-0-0-0-0-0-0-0-0

"Alright David where are we going?" Emery asked only sounding half concerned as he drove her to a location only known to him.

The blue eyed newsie smiled knowingly to himself as he turned another street corner and onto the highway. The red head looked out the window at the street signs as they pulled onto an on-ramp that led them well out of their borough and toward the city. Brooklyn in particular, this was the way to the Brooklyn bridge she at least knew that. What she didn't know was what David had planned that involved them venturing out into Spot Conlon's old territory. She knew he had been trying to make up for all the dates-gone-awry but she didn't think he would go so far as to take them all the way to Brooklyn for another one.

As they drew closer and closer toward the bridge she could feel the pressure start to settle itself onto her shoulders and she began to get nervous. She felt bad having him take her to all these fancy places like the theatre and fancy restaurants only for him to find out that she didn't have as good a time as he'd hoped. It wasn't that the places weren't fancy enough for her, she felt too much pressure to have a good time and to behave a certain way and that she couldn't be herself in these high class places. Not this time, no matter what it was she was gonna man up and love it because David deserved that much. What good is it to do all this nice crazy stuff for an ungrateful girlfriend.

She swallowed nervously and looked out the window as they finally crossed the Brooklyn bridge in all it's glory. _Get a grip! It's not like I'm getting arrested, it's just a nice date with my sweet boyfriend. Definitely no means for flipping out at all. _Emery shook her head and relaxed her shoulders as she leaned back into her seat and let out a small breath. She reached for the dial on the radio and turned it to a easy listening station that was playing a Hall and Oates song.

"Nice choice m'lady." David said, his half smile growing wider as he switched lanes.

Emery smiled and looped her arm through his and leaned on his shoulder. She giggled when he started to hum the song, she liked the way the deep sound resonated in his chest and made a slight buzzing noise in the back of his throat. The mood seemed to lighten up as they turned onto a road that lined up with the river and David took a round about down a ramp toward a two lane road. It didn't take her too long to realize where the road was taking them and her began to stomach flutter nervously. David pulled into the parking lot of an old boat house and once he powered down his car she knew he could feel Emery go rigid.

She didn't want him to know she was starting to feel so hesitant so she let go of his arm and sat up to unbuckle her seat belt. David met her on the other side of the car and helped her step down and out of his truck. She looked up at him and gave him a timid smile that her returned with warm grin. He took her by the hand and led her down a very familiar path toward some docks. These were the same docks they use to play on when they were kids and when Spot owned this territory.

Emery's heart beat spread a light tingle through her body as she looked around at all the familiar surrounds and nostalgia washed over her. Jack had taken her here a little while after they had first met along with some of his boys, David included, to swim one summer when they simply couldn't find any other way to beat the heat. David had pulled her out from under another kid that had jumped on her in these very waters below this dock. The kid didn't mean to, but when he jumped in he hadn't noticed Emery and almost drowned her in the process. If it weren't for him she might've have gotten seriously hurt or even worse...

The thought made her shudder and she pulled herself closer to David and clung to his arm. He took it as her being cold from the chill of the night and urged them further down the dock until they reached the very end of it where a bare blanket had been laid out. Emery could've flown she was so full of joy as they settled down onto the blanket with the night sky reflecting onto the gently moving water of the river. The moon seemed as if it were right on the horizon as it hung lazily in the sky, glowing brilliantly and in full.

"Oh David..." She breathed out in utter astonishment as she let her eyes rake over the lovely scene that surrounded them before settling on his face.

He smiled as he cupped her face with his large, warm hand. She leaned into the touch and let her eyelids flutter half way down her bright green orbs. The redhead found herself teeming with delight as he placed a soft kiss on her forehead, then her nose and both her cheeks. Just as he was about to put a kiss to her lips she found herself stopping him and glancing to the side.

"I'm so sorry about our other dates David." She almost whispered as she brought her hand over his as it still held her face.

He shook his head. "Don't think about them now, I wanted to do something special for you and I finally found out how."

Emery felt his words forge deeper into her as he spoke in that soft tone and she wondered if he could feel it too. Before she knew it she was leaning up toward him and planting a light kiss on his lips and let out a small giggle of amusement despite her flushed cheeks as she saw the astonishment in David's eyes reach the rest of his face. He raised a brow at her, his blue eyes exuding an emotion that seemed to make his eyes burn though she didn't know quite exactly what it was.

"David?" She queried as he shifted a little.

Suddenly she was pushed down onto her back and a pair of lips were being pressed against hers in a heated kiss that took her completely off guard. David pulled away from her and smirked as he hovered over her now trembling frame and beet red face.

"You know, I don't think you realize quite how lucky you are Emery McKlenahan." He said in a voice that made Emery shudder.

"A-and why's that?" She managed to stammer.

He chuckled and pressed his nose to hers lovingly as he kept her gaze. She felt his arm come up under her to cushion her head as well as to support his weight while his other one wrapped around her waist. Emery tried her hardest to stop herself from shaking but she couldn't help but found it particularly hard as he moved his lips toward her jaw and down to her neck to place heated kisses on her sensitive skin. David was so close to her, he had never been so daring before and all these new sensations were overflowing as her heart threatened to beat out of her chest. The red head let out a shaky breath as his lips grazed back up her jaw before he pulled away completely.

"After so much trial and error I almost gave up and asked Spot where to take you on our next date." He admitted looking away from her glazed orbs out of pure embarrassment.

Emery brought one of her small hands to his face and rubbed his cheek with her thumb. When he brought his gaze back to meet hers she gave him a small smile that grew even wider when he grinned at her too.

"But you're my girl, not Spot's, so I figured it out and here we are. Do you like it?" He asked, the shrinking tone in his voice almost breaking her heart.

She nodded and wrapped her arms around his neck, gently running her fingers through his curly hair. "Of course I do, I love it so much David."

She watched as his eyes fluttered shut and he leaned into the touch, pulling her closer toward him as she giggled at the gesture. He had always liked it when she raked her fingers through his hair like that, almost like scratching a dog behind his ears, and it had always amused her to see him react the way he did. She swallowed lightly as she brought her hand back down to the nape of his neck causing him to open his eyes, the brilliant blue in his orbs full of confusion.

"I-I...I love you David." Emery finally managed to say, her heart skipping a beat and her face lit up like the fourth of July with the color red.

He was silent for moment simply because he was stunned but soon enough he found himself kissing her, differently from before. This kiss was one full of passion with the heat that radiated from both their faces as it continued. She nearly jumped out of her skin when his tongue brushed against her bottom lip and even more so when she granted him entry. Her head went fuzzy for the few moments that he timidly explored the cavern of her mouth before she found herself completely breathless. Taking a hint he pulled away from her and allowed them both some room to breath.

Something rose in his chest as he looked into her eyes, soaked in the appearance of her flushed cheeks and soft pink lips that were slightly parted. Hot breath intermingled as they took a moment to come down from the momentary high they had supplied to each other. David rolled onto his back and pulled Emery closer to him and felt on top of the world as she cuddled closer to him, wrapping an arm tightly across his chest. He placed a hand on top of hers and interlocked their fingers lovingly.

"I love you Emery." His words echoed in the empty space of the night air.

Emery was thrilled beyond belief to hear those words and it sorely made her want to kiss him again like they had been before but at the moment she felt extremely content in being held so close and so tenderly by her sincere and loving boyfriend. As she reveled in his warmth on the soft blanket she couldn't help but smile when she thought about how he would most likely boast about how successful he had been to Spot as soon as he got back to the apartment he shared with the Brooklyner, Jack and Kid Blink. She couldn't blame him, this had been one of the best nights of her life.

"Hey David."

"Hmmm?" David hummed in response as well as content.

"Let's come here again." She murmured sleepily as she curled further into his side.

She felt her smile spread further as he instinctively pulled her closer and heard his soft reply.

"Of course."

**Yeeeeeeeeaah I'm not super great at endings and I'm gonna be honest I totally winged this one. If you liked it though I'm really glad that you did! :D Hope to see you as I continue to update my other story and I apologize for the delay .-.'**


End file.
